Sodium Hydroxide → HCID 178484233、化合物

HRID 1922414ノート

反応式

HRID 1922414 の反応式
[CH3:1][N:2]([CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=[O:32])C(=O)OC1C=CC=CC=1.[OH-].[Na+]>CCO.O>[CH3:1][NH:2][CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=[O:32]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 178484234Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

生成物 1

HCID 178484233HCID 178484233、化合物

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate (700 mg, 1.56 mmol) was stirred in EtOH (20 mL). To this suspension was added solid NaOH (624 mg, 15.6 mmol), followed by water (10 mL). The flask was then fitted with a condenser and was heated to reflux for 2 h. When TLC analysis showed that the reaction was complete, the mixture was cooled to room temperature and diluted with water. The product was extracted with dichloromethane (3×) and the combined organics were dried, filtered and concentrated, then chromatographed in EtOAc, followed by 10% 2M NH3/MeOH in dichloromethane. The isolated spot was then triturated with methanol and ether. Yield (223 mg, 43%). 1H NMR (DMSO-d6) δ 7.73 (d, 1H, J=3.6 Hz), 7.59 (d, 1H, J=5.4 Hz), 7.10 (m, 2H), 6.73 (m, 2H), 6.45 (brs, 2H), 3.91 (t, 1H, J=7.2 Hz), 2.81 (t, 1H, J=7.2 Hz), 2.65 (t, 1H, J=7.2 Hz), 2.50 (t, 1H, J=7.2 Hz); ESI-MS (m/z, %): 329 (MH+, 70), 149 (100), 141 (80), 127 (96).

後処理

  1. customThe flask was then fitted with a condenser
  2. temperaturewas heated
  3. temperatureto reflux for 2 h
  4. extractionThe product was extracted with dichloromethane (3×)
  5. customthe combined organics were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed in EtOAc
  9. customThe isolated spot was then triturated with methanol and ether
  10. customYield (223 mg, 43%)

出典と根拠

ORDレコード
ord-8eeb00cb81614f3a8408e6d33bb8da0b
出典データセット
uspto-grants-2012_05
特許番号
US08173813B2

反応ノート

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